PreviousNext property

$195 / night

$195

Wonderful Craftsman-style FARMHOUSE built in 1912 and BUNKHOUSE on a working horse ranch just 3 minutes from downtown Ashland, home of the renowned Shakespeare festival and Britt festivals in nearby historic Jacksonville.
'FARMHOUSE' has 4 bedrooms and 2 full baths. All rooms have queen beds for $295/night high …

PreviousNext property

$85 / night

$85

Private cottage apartment with full kitchen and living area adjacent to family home. Covered porch and garden area to enjoy. Less than 15 minutes to Shakespeare Festival and downtown Ashland. Fresh eggs, local bread, jam, 1/2 and 1/2, milk and butter are stocked in fridge. There is also Nespresso, coffee and tea for …

PreviousNext property

$135 / night

$135

We are located in the heart of Ashland. Only 2 blocks from Downtown. Enjoy the open Garden and Great location to all Restaurants, Shops, Theaters and Local Sporting Events. We are 3 blocks from University of Southern Oregon. Full Kitchen, Bedroom/Queen, Wall mounted reading lamps and TV.
The Cottage comes with …

PreviousNext property

$285 / night

$285

Fully restored vintage cottage in a quiet neighborhood just steps away from downtown Ashland and the theater. Surrounded by lovely gardens assuring a private and serene environment. The cottage is tastefully decorated , is immaculate and has 2 bedrooms, 2 baths, office, full kitchen, front porch and outdoor patio…

Restful, relaxing, rejuvenating!

Left on Nov 28, 2011 for a stay in November 2011

Staying at the Box R Ranch is a very unique experience!
The privacy of staying on a ranch, in a beautifully constructed log cabin, is so peaceful. If you bring enough food up from ashland, there is no need to go anywhere else. You can hike the trails of the 1500 acre ranch at your own level...some trails are strenuous and others pleasantly level. We love waking up to the sight of cattle …

Be wary of this property and owner

I do not recommend this property. It is a nice 1/2 duplex convenient to downtown Ashland but the owner lives in the other 1/2, was hard to deal with and in the end turned abusive toward me.

Among other things we had a miscommunication about the final cleaning of the house. The owner came over the morning we were leaving (she "popped in" every day of our 4 day stay) we went over what she wanted…

$160

SPECIAL; August 29 -September 2nd 5 days for the price of 4
Find Ashland Vacation Rentals on FlipKeyWelcome to the ArtYCottage nestled in the Cascade foothills, minutes from downtown Ashland, Oregon, home of the Oregon Shakespeare Festival and Saydah Design.
All of the work in the Artycottage is made by …

Beauty and Comfort

Left on Jun 24, 2012 for a stay in May 2012

The artycottage was the perfect choice for our stay in ashland. We were surrounded by beauty and comfort from the moment we entered the cottage until we left ll days later.
Tom and Margaret Saydah have created a completely unique environment. Every detail of the cottage has been artfully designed and expertly crafted. The fine wood and metal work, beautiful furniture, hand made textiles…

PreviousNext property

$150 / night

$150

Second Spring Property
We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014.
This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3 bedroom 2 bath home or …

$165

Set in Ashland's best neighborhood, this 1931 cottage has been lovingly restored and set up to address your every need. Cozy and incredibly clean, filled with art, hand-made pottery, antiques and hand crafted furniture. Comfortable beds, high quality linens and a fully equipped kitchen. A truly amazing property with…

BEAUTIFUL COTTAGE AND GARDEN WITH EXPERT ATTENTION TO DETAIL

Left on May 06, 2012 for a stay in May 2012

We had a fantastic time staying at the High Street Cottage. It was spotlessly clean with all the necessary amenities. We were greeted warmly by Elizabeth and given a tour of the cottage upon our arrival. There was even a yummy gift in the refrigerator! The garden was breathtaking and we were even offered fresh greens from it! We loved all the decorative touches with her pottery in and out of …

PreviousNext property

$225 / night

$225

Relax, refresh and "reboot" for a log cabin farm or ranch vacation at the pristine Green Springs Box R Ranch in the Southern Oregon Cascade Mountains. We raise all natural grass fed Angus beef year round and are open to the public for farm ranch stays holidays 2013 from Nov. 20th through Jan. 5th, 2014 and Memorial…

Amazing little private retreat in the trees...with a great deck

Left on May 09, 2012 for a stay in May 2012

This is the pefect little retreat for two (or 3 or 4 with the hide a bed in the living room) which sits up on Tolman Creek Rd., with amazing views over the valley and into the trees on two other sides. The owners really have made sure the little details were taken care of, like good coffee (Starbucks!) a selection of teas, nice selection of Cd's to go with a great sounding portable stereo, a gas …

PreviousNext property

$225 / night

$225

Welcome to Lori Lane Cottages! You are looking at our 2 bedroom, 1 bath cottage, formerly The Bayberry Inn Cottages.
Newly built for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic …

PreviousNext property

$150 / night

$150

STAY
Overlooking beautiful meadows, the light filled studio sleeps up to six with two queen beds in the loft spaces and a futon downstairs. The Farm Stay also features a wood stove and a full kitchen stocked with dry goods. Select perishables, fresh produce, and farm-grown goods from our grocery list and they'll be …

$160

Nestled into one of Ashland's best neighborhoods, the Terra Cottage Inn is a clean and beautiful, hand-crafted artists' cottage. Full of art, hand thrown pottery, custom built furniture and all the amenities to make this a true luxury experience. Quality comfortable beds with high thread count linens, spa robes, …

Luxury Home away from Home

Left on Mar 19, 2012 for a stay in March 2012

This rental has everything a traveler could want or need. The apartment is beautiful, peaceful and very comfortable. The fact that everything was up to date and in perfect shape added to our enjoyment of our stay.

PreviousNext property

$250 / night

$250

Meadow House, built in 2000, features natural wood and plaster throughout, a well-stocked cook's kitchen with fresh eggs and milk in the refrigerator, and the quiet of off-grid living. The three bedroom, two bath house sleeps up to ten comfortably with 3 twin beds in the West Bedroom, a queen bed and single futon in …

PreviousNext property

$80 / night

$80

Arbor Studio is a compact, tidy single building just right for one person, very intimate for two.* It's nestled under a grandmother grapevine and looks out into our in-process healing garden.
Expect friendly atmosphere, interior cleanliness, bamboo floors, interesting lighting,filtered drinking water, a moderately …

$100 / night

$100

Lhasa House is a charming studio cottage with unique privacy and its own street entrance. It is located on the perimeter grounds of a vintage house built in 1884. The property’s interior gardens are developing into a healing sanctuary (accessible to guests Summer 2014). The owners are yogic body-mind healers in …

Quiet, convenient, tasteful value

Left on Jul 10, 2013 for a stay in July 2013

We spent 3 days here, and found it a very peaceful, restful place. It is one larger room with an Ikea sofa/bed and chair/bed, they were perfectly comfortable. There is a vestibule at the front door with convenient hooks for coats and hangers and room for luggage. There is an armoire as well. The kitchen is small and tight but works fine. Parking on the street right next to front door, never had …

PreviousNext property

$500 / night

$500

1 Bedroom
1 Bathroom
Sleeps 3
This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3 bedroom 2 bath home or split into two connecting apartments with kitchens, dining areas and living rooms. You can …

$150

Abigail's Cottage is licensed by the city of Ashland (Business License #007411 & Planning Action #06-275) and Jackson County, (#1581566C) and meets required health, safety and fire codes.
Please note: Rates do not include food service and we do not accommodate pets.
Non-smoking, two bedroom 1 1/2 bath cottage, …

Fabulous place to stay!

Left on Oct 08, 2011 for a stay in September 2011

We recently stayed in this cottage for 3 nights and we really enjoyed ourselves. The short walk to the plaza and theaters was ideal, but we were most impressed by how clean and well-maintained the cottage was. The cottage is on the property of the Hersey House Bed and Breakfast Inn and the hosts were very welcoming, and they deliver a morning continental breakfast tray. We especially liked the…

$149 / night

$149

A“lake cabin” vacation can become a reality at Hyatt Lake Resort, approximately 22 miles east of Ashland on Rt. 66. The forest surrounds the cabin, which is located at “Campers’ Cove.” From the front deck you can BBQ while viewing the lake, enjoy the Jacuzzi or just sit and watch the eternity of stars in …

Beutiful Cabin and Great Staff

Left on Aug 26, 2014 for a stay in August 2014

My girlfriend and I were extremely impressed with campers cove. The cabin was so clean, comfortable, and had every amenity you could imagine. A BBQ, Jacuzzi, ect. The staff was also incredibly friendly.

On our first night I somehow locked us out of the cabin. Both my girlfriend and I were stuck in the cold with no keys, not even our car. I was afraid we'd have to sleep in the jacuzzi to keep …

$250

The Green Springs Retreat is a spacious log cabin home situated on 5 acres of quiet forested property in the mountains above Ashland, Oregon. We have 3 bedrooms, 2 bathrooms, and a loft space that can comfortably sleep 4. The master bedroom has an antique oak framed queen bed with a spacious closet and private …

Truley An Unexpected Retreat

Left on Jul 24, 2014 for a stay in June 2014

We did not expect to stay so far out of Ashland. We were just stopping one night on our way to Coos Bay. Having misread the directions, we ended up driving @ 25 minutes up from Ashland to what we found was a lovely place once we got there, and a welcome diversion from the city. This Hotel seemed to be a hub for biking, hiking , and other adventures. A rustic setting, however, the accomodations …

PreviousNext property

$180 / night

$180

Beautiful log cabin in the Southern Oregon Cascade Mountains. Located very privately on 160 acres of mountain meadowland. Cabin sleeps up to 8 people. Full kitchen, full bath down and half bath up, hard wood floors, wood stove, front porch where you can sit and watch for wildlife. Fresh air, sparkling stars, …

PreviousNext property

$250 / night

$250

Helman Guest House is a charming early 1900's two bedroom home that can comfortably sleep up to 5 guests. It is only three short blocks from Ashland's Plaza, restaurants and Oregon Shakespeare Festival theaters.
The large master bedroom, located on the ground floor, has a luxurious king-size bed, its own television, …

Comfortable and close to the theaters

Left on Jul 15, 2013 for a stay in July 2013

One of the best aspects of this house is its layout. There are several distinct areas for people to be: dining room, living room, kitchen nook, front porch...allowing four people to spread out with books, projects and conversation. Furnishings are acceptable but not grand. Sheets and towels likewise. Beds are comfortable. The kitchen is basic but adequately equipped for simple meals. There is no …

PreviousNext property

$225 / night

$225

Welcome to Lori Lane Cottages! You are looking at our 2 bedroom, 1 bath cottage, formerly The Bayberry Inn Cottages.
Newly built for modern comfort, the Lori Lane Cottages are only a short walk from the Oregon Shakespeare Festival (OSF) and downtown Ashland, where you can experience world class shopping and fantastic …

Charming spot

Left on Jul 23, 2014 for a stay in July 2014

I took my 86 year old mother with me to visit Ashland. The cottage was very clean and cozy and my mom was delighted. There is no real living or dining space inside but the outdoor table and chairs provided the seating for meals that we need and we prefer to sit outside anyway. The gardens are very well kept, and the owners helpful. The off street parking is very convenient. It is also an easy …

PreviousNext property

$225 / night

$225

Second Spring Property
We are excited to announce that our property was given The Ashland Historic Preservation Award in 2014.
This luxury vacation property is uniquely designed for elegance and comfort that will make you feel right at home. This newly renovated craftsman can be rented as a 3 bedroom 2 bath home or …

$165

Relax in this rural setting tucked into the the foothills of the Siskiyou Mountains with room to roam. Little Creek Ranch is a beautiful 20 acre horse ranch just a couple of minutes from downtown Ashland. Enjoy the trails, creek, fishing pond and endless views in all directions. Visit one of the several well-known …

Peaceful ashland Respite

Left on May 23, 2011 for a stay in May 2011

We travel from Seattle to California a couple of times a year and we always stop and stay with Debbie at Little Creek Ranch. Her hospitality is welcoming, and the cottage is full of country charm located in a gorgeous farm setting. Little Creek is located very close to downtown ashland and its many wonderful restaurants. This property is ideal for folks traveling with their well behaved dogs…

I found the DeLaunay House to be a charming and relaxing retreat

Left on Mar 30, 2011 for a stay in March 2011

If you want amenities, but also desire the charm and character of a time from days gone by, then you have arrived when you enter the DeLaunay House. The attention to detail creates a harmoniously beautiful retreat. The Wrap around porch is a great place to enjoy the small town environment. The central location puts you where you want to be: close to all and yet in a world all your own (…

PreviousNext property

$395 / night

$395

The perfect location for your next family rendezvous, art retreat or special occasion. There are numerous gardens and the park like setting is lush and shady with ample space inside and out you will always find a quiet place to enjoy all the property has to offer.
The Property benefits from a hill top location …

About Us

Love for FlipKey

As featured in USA TODAY and recommended by Travel + Leisure in its annual Villa Guide:

FlipKey Elsewhere

New to FlipKey?

FlipKey is a vacation rental marketplace with more than 300,000 rentals around the world. Find the perfect place to stay for your trip, and get great value along with the space, privacy and amenities of home.